2024 Sailing Season is coming! See you April 13, 2024!


Running Free Inc. has multiple facets to the business of running the Schooner Woodwind and Woodwind II and the docks at the Annapolis Waterfront Hotel/Pusser’s Caribbean Grille.

Employment opportunities may include:

  • Event Sales Associates
  • Administrative Assistant
  • Event Sales Manager
  • Waterfront Facility Manager
  • Office Manager
  • USCG Licensed Captains
  • Crew Members/Deckhands
  • Dock Staff at the Annapolis Waterfront Hotel
  • Customer Service for Ticket Sales and Dock Space

Current Openings

Schooner Woodwind & Woodwind II are identical 74-foot sailing yachts available for public sailing and private charter departing from the Annapolis Waterfront Hotel.

Schooner Woodwind also manages and maintains the 360 feet of wharf side dock space (available for transient dockage) on behalf of the Annapolis Waterfront Hotel.

Since 1993 the Woodwinds have been a family-owned and operated company.

Offsite Office
1930-A Lincoln Drive, Annapolis, MD 21401
(Monday-Friday, 9-5)
Onsite Office & Boats
80 Compromise Street, Annapolis, MD 21401
(Everyday, April 15-October 31)
(410) 263-1981
Schooner Woodwind